Maximum Security
by istheresuchathing
Summary: Dean Winchester, accountable for three cases of theft, eight credit card scams, and two cases of murder. He's just a regular convict in a regular prison. That is, until he starts up a huge riot and is forced to be placed in a cell, with maximum security needed. Castiel Ingram, prison guard that's usually reserved for the baddest of the bad. Castiel Ingram, meet Dean Winchester.
1. Chapter One

Dean Winchester, accountable for three cases of theft, eight credit card scams, and two cases of murder. He's just a regular convict in a regular prison. That is, until he starts up a huge riot and is forced to be placed in a cell, with maximum security needed. Castiel Ingram, prison guard that's usually reserved for the baddest of the bad. Castiel Ingram, meet Dean Winchester.

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This is an AU where Dean is a criminal and Castiel is a prison guard. Based off of a Tumblr prompt.

 _Coming soon!_


	2. Chapter Two

Castiel Ingram was just lounging in the break room, eating the honey glazed doughnuts that were offered to prison staff members daily when his walkie talkie crackled to life. "Ingram!" the voice on the other end barked. Quickly stuffing the rest of the doughnut into his mouth, Cas pressed a button on it to reply. "Yes, this is Castiel Ingram. What's going on?" he asked, wiping the crumbs on his mouth and hands with a napkin. "Riot in the cafeteria! Get your ass down here now!" the voice yelled, trying to be heard above the screaming and noises in the background. Castiel's eyes went wide. _A riot? There has never been a single riot in the Green River County Detention Center._

Running through the halls, it was eerily quiet and there was no other sound than his footsteps and the distant sound of fighting and yelling. As Cas was running through a dimly lit corridor, he thought he saw a flash of orange speed past him. He suddenly stopped and turned to see a convict running the other way, towards the break room which led to the exit of the detention center. Immediately forgetting about the chaos in the cafeteria, Castiel chased after the convict.

Cas was certain that the man would never make it to the exit since he didn't know the way out nearly as well as Castiel. But strangely enough, the man seemed to know exactly what he was doing. Castiel had only been hired for a few months and letting this convict outrun him would probably end his career as a guard. Determined, Cas sped up and began to draw closer to the running man.

* * *

Dean Winchester was sitting alone in the cafeteria, before exchanging glances with Benny Lafitte, another convict. He nodded once and Benny knew it was go time. He suddenly punched the burly man next to him hard on the jaw. Before Dean knew it, there was a full blown riot in the cafeteria and the guards were hurriedly calling for backup. Dean had to get out before more guards came. But before he could, a thin man with a bleeding nose approached Dean from behind. He was about to wrap his hands around Dean's neck when Dean suddenly lashed out with a back kick and the man collapsed. "Maybe next time, Alastair." Dean winked cheekily before darting out of the cafeteria.

He was running through the halls when another guard suddenly blurred past him. Dean turned around once to look if the guard had noticed him and he saw a figure stopping and turning towards him in the dark corridor. Dean turned his head back so quickly it could have given him whiplash. He heard light but quick footsteps sounding from behind him and knew the guard was chasing him. He started to panic a little. Trying his best to remember the blueprint of the prison, Dean turned a corner and ran down a left corridor. _Or was it right?_ He couldn't afford to hesitate or make a single mistake otherwise he would be put in a cell with maximum security. Making it even harder to escape. _But not impossible._ Dean smirked to himself when he saw a brightly lit room that smelled of coffee straight ahead of him. _The break room._ He remembered this from the map. After this would be. _Freedom_. He was going to make it. He was going back home. Back to his brother Sam and mother, Mary. He was going to make it.

And that's when everything went dark.

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Hi, I hoped you all enjoyed this first chapter! This story was based off a Tumblr prompt and I have been wanting to write this for a long time! I will update regularly, maybe thrice a week or so.


	3. Chapter Three

Dean woke up in a strange room, a dull ache on his left side slowly ebbing away. He looked around. This wasn't his normal cell. Where was he? As if someone had been listening to his thoughts, a voice answered him. "If you're wondering where you are, you've been placed in a single cell, with maximum security ensured. So you might not want to try that stunt you tried to pull today again." Dean searched for a face to match the voice but the dim light wasn't really helping.

Eventually, he saw a pair of blue eyes that seemed to glow in the dark room. "I didn't try. I _did_ do it." Dean growled, hostility radiating off of him in waves. The eyes continued to stare at him, unblinking. "Yet you're still here." the man replied calmly. His voice was low and husky, and although Dean wasn't sure if voices could be called attractive, this one definitely could. Dean glared at the dark figure of the man. "Only because you used a _taser_! You shouldn't have used that!" he yelled angrily, and it was true. Prison guards weren't supposed to use tasers on the convicts. "You were going to get away and I had to stop you. We are allowed to use tasers if necessary. And _this_ , was a very necessary situation." A handsome, dark haired man stepped out into the light where the rays of the moon hit him. Dean's breath hitched in his throat as he admired how the moonlight shone on the man at an unnatural angle, his sharp and attractive features blending with the dim light. His blue eyes, that appeared silver from the moon, flickered with amusement. "So, what, you're my new babysitter?" Dean asked sarcastically, trying to hide how much he was affected by those blue eyes. "Well, yes I suppose I am. But you'll be charged with a new crime to add to your record since escaping is a felony offence. Your trial for that charge is in three days." the prison guard told him. Dean shook his head. "You sound just like a walking book of the law, you know that?"

The man frowned and opened his mouth to retort when his walkie talkie crackled to life. "Ingram! Get your ass down here pronto! We're gonna have a meeting!" the harsh voice on the other end barked. The man sighed and pressed a button. "Coming." he responded. "Ingram, huh?" Dean smirked. The guard turned towards him and rolled his eyes. "Yes, my grandfather was English and I decided to take his last name." he explained. Dean nodded. "You got a first name?" he couldn't help but ask. The man got up and glanced at Dean quickly, debating whether to say it or not. "Castiel." he mumbled before grabbing his trench coat from a hook on the door. "Later Cas." Dean called out after Castiel and he turned towards Dean, giving him a strange look but gave him a quick wave before he disappeared into the hallway.

Dean smacked himself in the head. "What the hell was that?" he demanded aloud. "This guy tased you and then you get one look at him and you become his lap dog? Get a hold of yourself!" Dean exclaims and slumps down on his cell bed.


	4. Chapter Four

Castiel hurried through the empty corridor, already late to the meeting. But instead of panicking about what the head might do to him, he found himself having curious thoughts about the new convict. Cas had opened up to him far too easily when he was meant to be giving the prisoner a stony silence. It was just... Castiel expected a crazy madman who preferred to fight rather than talk. What he didn't expect was a gorgeous convict, who, after getting over the initial and expected anger, was rather friendly. He wondered how this charming man was actually guilty of several murders, as well as countless numbers of identity thefts. But then again, the best psychopaths are the charming ones. Cas reminded himself that, despite however much superficial charm and normality the prisoner projected, he had lacked in empathy, guilt, and love. This man, this Dean Winchester was really a cold blooded killer.

The meeting room's door burst open and Castiel ran inside. "Sorry I'm late sir." he apologised to Uriel, who was in charge of the prison while Chuck was in the hospital, in a coma. The place had been hell since he left and in just the past month, there has already been one riot and an escaped prisoner who was only caught last week by the police. Uriel glared at Cas, making him shrink a little on the inside. "Next time, I want you to be here when you're supposed to be here, got it Ingram? Do you think you can get it through that thick skull of yours?" he barked, scowling. "Yes sir." Cas replied calmly. He had been a guard for about three months and he had been fine with his job until Uriel took control.

"Good. Now take a seat." Uriel commanded and Castiel sat down next to his friend Charlie and brother Gabriel. "Now since Charles here was late, I guess I'll have to repeat myself again." Uriel said, turning to address the collective crowd again. Castiel would have loved nothing better than to sock Uriel across the jaw right now but he forced himself to stay put and gritted his teeth instead. "Well that's a new one." Charlie muttered, nudging Castiel's shoulder playfully. "Maybe I should add that to my nickname for Cassie collection." Gabriel whispered jokingly, earning a small shove from Cas. His friends were probably the only reason Castiel was still here.

"As I was saying, since that riot in the cafeteria which was barely held under control, I'm making you all do an intensive two week physical training unit starting tomorrow morning. With your assigned prisoner. They'll be doing it with you so you all can learn how to control them better." This caused a ripple of disagreement and murmurs to spread across the room. "What the hell? No way am I working with Gorilla Fists!" Gabriel whispered loudly, his eyes wide with fear. "You know there's a reason why they call him that!" "You have other convicts you guard." Castiel reminded him. "That doesn't help. Have you seen any of them?" his big brother demanded. "I can relate," Charlie replied. "The guy I'm probably gonna get paired with is called Pickpocket Pete. He stole my gum the last time I checked on him!" she complained. "Well, Pete's only there for theft so he probably won't maul you to death at least." Gabriel argued. Charlie was about to retort something when she noticed how quiet Cas was.

"So Castiel, do you want to add anything about that hot new prisoner of yours?" she asked slyly. Cas squirmed uncomfortably under the combined suspicion and amusement of Charlie and Gabriel's stares. "No." he answered, because there really wasn't. Castiel knew he wasn't supposed to be all buddy-buddy with a convict but he didn't mind having to do the course with Dean. "Right. Because there isn't anything to complain about, hmm?" Charlie hinted jokingly, wiggling her eyebrows suggestively. "Well, nothing except for his record." Cas replied, reminding himself that Dean was a criminal, not a friend.

"Alright! Shut it people!" Uriel yelled, trying to control the volume in the room. After a few moments, the room calmed down and allowed him to speak again. "Now the night guards are about to come for the night shift so all of you are dismissed."

Everyone began to stream out of the door and as Castiel was about to leave, Uriel blocked his way, a wicked look on his face. "Except for _you_."


	5. Chapter Five

Castiel found himself walking on the path back to Dean's cell after a quick round on all of Block B's cells. When he arrived, he was surprised to find Dean still awake. "Lights went out about forty minutes ago." he told the prisoner in a stern tone and Dean slowly lifted his head, completely unfazed by the change in tone. "I couldn't sleep." he replied flatly and looked at Cas. "Why are you stil here? You have to work the graveyard shift too?" he asked Castiel and the other man sat down on a nearby chair. "Uriel hates me." he answered simply. It was obvious to Dean that Cas felt he wasn't being authoritative enough and decided the cold shoulder was the way to make up for it. He shrugged and turned back to the only possession he had, a worn magazine he was allowed to bring. Dean didn't really feel like reading it again. He had flipped through 'Busty Asian Beauties' more times than he could count. But it was probably the only that kept him from dying of boredom ever since he had been moved to a high security, single person detention cell. As he turned to page eight, the pullout page with his favorite black haired beauty on it, he could literally feel the hesitation Castiel was feeling. Cas wasn't sure if he would rather sit there quietly and watch Dean for two more hours or actually talk to him. But he was afraid that Dean might use that charm and wit on him again and he would open up again. Nope, not this time.

Dean smirked from his position with his back facing Cas. He knew that Castiel was struggling to ignore him and continued to study the page. The corners curled up slightly and there was a permanent crease on a corner, but other than that, the page was in pretty good condition. Especially considering how Dean had had it for two years. Man, Rachel looked especially hot tonight. Dean couldn't remember the last time he had jerked off but planned to tonight after Cas left. But after another thirty minutes of silence, he frowned. Dean couldn't believe that Cas' will to not speak was still holding up. He turned around to see Castiel fidgeting in his seat. Grinning, he decided to finally break the ice. "You gonna ignore me forever?" he asked smartly. Cas glanced up quickly, a little startled before replying. "I didn't ignore you. I just don't want to talk to you." _Ouch_. But nonetheless, Dean continued. "Come on Cas. I'm bored. And I know for a fact that you're bored too."

Castiel sat up straight in his chair. "I'm not bored at all. I am accustomed to this silence." he answered quickly and proceeded to prove his point by staring at a wall intensely. Dean chuckled quietly. This guy was a riot. "Well we'll see how long you hold up." he said and watched Castiel. After a few minutes, Cas began to fidget again. The wall was much less interesting than anything else in the room. _Why couldn't he have picked something else to prove his point?_ He could feel a pair of bright green eyes staring at him. Finally unable to stand it any longer, he turned to face a very smug Dean. "Now you wanna catch me up on the prison gossip?" he asked cheekily.

* * *

"So I'm gonna have to do the course with you?" Dean questioned, wanting confirmation. "Yes." Castiel answered, before glancing at Dean for his reaction. But instead of groaning or getting angry, the green eyed man just smiled and shook his head. "You know, I'm feel pretty honored that the boss man actually dedicated this entire thing to me after what I did." he joked and Cas couldn't help but crack a small smile. Dean was surprised and kind of happy when he saw Castiel smile. He'd never seen the man smile before and the grin on his face was amazing. He could've melted a person with that smile. "You should smile more." Dean told him, before realizing what he said. Castiel blushed lightly but Dean couldn't see since the lighting was dim. "Alright." he replied and checked his watch in embarrassment. Only ten minutes left. Time really had flown when he was chatting with Dean. "I should probably go check up on the other prisoners." he informed Dean quickly. "Goodnight Dean."

"Night Cas." Dean bid Cas goodbye as the blue eyed man left. The room felt a lot colder and lonelier after Castiel shut the door. Dean couldn't seem to find that urge he had earlier to masturbate and decided it was because his chat with Cas had been draining. A tiny part of him knew that wasn't the reason but Dean didn't allow it to probe any deeper. Calling it a night, he lay down in his cell bed. He needed some rest if he wanted to do well in the training course tomorrow.


	6. Chapter Six

"Gabriel Ingram?" Uriel's voice boomed over the courtyard as he surveyed all the prison guards and handcuffed convicts that were standing in neat rows in front of him. "Here." Castiel's brother lazily waved an arm around. Uriel gave him a disapproving look but didn't comment on his lack of formality. "Your assigned partner was Raphael Thanatos. Is he present?" he demanded and Gabriel jerked a thumb at Raphael. "Yeah he's here."

Checking the man's name off, Uriel moved on to the next name. "Castiel Ingram." he called out, barely veiling the distaste in his tone. "Present." Castiel said and raised a hand up. "Your assigned partner was Dean Winchester. Is he present?" he questioned and Cas was about to reply when Dean spoke up himself. "I'm here, as you can see." the green eyed man said sarcastically and a couple convicts and even a few guard chuckled. Uriel glared at him. "Shut it Winchester! Ingram, keep him under control!" he commanded, not bothering to hide the contempt in his voice this time. "Yes sir." Castiel replied, his face burning. Without another word, Uriel moved on to the next name. "The big man doesn't really like us, huh?" Dean whispered, leaning towards Cas. "Maybe you should let me do the talking next time." Castiel told him emotionlessly. Dean sighed. _Great._ He thought he had broken through a wall with Cas but it seemed like the man had ten more after that. Dean didn't really know why he wanted to befriend the blue eyed man so much, especially seeing as how Castiel was not nearly as eager. He gave a quick sideways glance at Castiel and saw those bright blue orbs immediately switch their attention back onto Uriel. Grinning, Dean turned his attention toward Uriel as well. _Maybe Castiel was even more eager._

* * *

"Now that attendance is done, I want to introduce two instructors who have agreed to help us during training." Uriel announced and two men stepped up on stage. One of them had blonde hair and bluish grey eyes while the other had brown hair and green eyes. Both looked very fit and Dean thought the brown haired man looked very familiar. "Balthazar," Uriel said, gesturing at the blonde man. "Is a fitness instructor of three years and our other volunteer, Sam, is a lawyer but teaches fitness classes in his free time." he introduced and Dean's eyes widened. That was his brother Sam up there. He looked so different than from the last time Dean saw him. The last time Dean saw him, Sam was a scrawny seventeen year old with short brown hair. Now the man standing next to Uriel was a giant with shaggy hair. Sam's eyes skimmed over the crowd, searching for someone. But as soon as his eyes connected with Dean's, his tight lipped smile spread into a full blown grin. Dean returned his joyful expression and gave him a thumbs up. Castiel, who was beside Dean noticed the gesture and his curiosity got the better of him. "Who's that man you're giving a thumbs up to?" he couldn't help asking Dean. Dean smirked at him. "Talking to me now, are you?" he asked cheekily, his mood was far too good to be ruined. Cas rolled his eyes good naturedly. "Yes, I'm sorry for ignoring you. But I need to keep up my guard image. Now are you going to answer me?" he explained to Dean apologetically. "Yeah okay. That giant over there is my brother Sam." he informed Castiel happily. Oh. Cas tried to ignore the relief he felt from Dean's answer. "Who is that fine piece of ass?" Gabriel whispered, nudging Castiel's shoulder. "That's my baby brother, you asshole!" Dean whispered back, furious. "You better stay away from him, pervert!" he hissed threateningly and Gabriel grinned. "Make me, big boy." he shot back, only half joking. Castiel decided it was time to step in and separate the two men. "Alright! Shut up both of you!" he warned them quietly, elbowing Gabriel further away. "But didn't you hear what he said about Sam?" Dean protested, still steaming. "Dean! Did you forget what happened last time you started a fight?" Cas reminded Dean and he opened his mouth to retort but Cas cut him off. "Not only that, but Gabriel is my brother and I will not hesitate to punch you if you lay a hand on him." he continued and Dean hesitated for a moment before standing back. "Whipped." Gabriel coughed rather loudly. And this time, Cas and Dean both gave him a sharp kick.

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I hope you all enjoyed this chapter! You're welcome for the early update and I actually have a reason. This story is going to become the main priority of my writing schedule now! I also wanted to thank Tiddo-mus for being super supportive and always leaving nice reviews!


	7. Chapter Seven

"Guards with A to M surnames, go with Balthazar to the tracks! The rest of you, stay in the courtyard with Sam and I!" Uriel ordered, barking out commands left and right. "Gabriel!" he suddenly shouted and the golden haired man froze, along with Raphael. He had been trying to sneak into Sam's group to get a first crack at the young trainer but Uriel had eyes like a hawk. He spotted Gabriel from a mile away. "Last time I checked, Ingram started with an I, not a M!" he yelled and pointed to the mixed group of prison guards and inmates who were gathered behind Balthazar.

Gabriel groaned but dragged Raphael to the other group quickly, mumbling something inaudible to himself. "You shouldn't have run off like that. You knew you were going to get caught." Castiel told his brother disapprovingly but Gabriel just grinned. "For someone that fine? I'd get caught a thousand times trying to get over there." he joked cheekily. "I'm gonna say this once more," Dean growled with narrowed eyes. "Stay. Away. From. Sam, you bastard." Fed up with their quarrelling, Cas decided to step up as the adult. "Both of you, stop acting like children. Dean, you have a right to be angry but you do know that Gabriel is only joking, right?" he said sharply. Gabriel smirked and was about to reply when Balthazar began speaking. "Now that everyone is here, I'd like to begin the training. We'll be starting off with fifteen laps around this track. I _will_ be timing you." he explained to everyone confidently, before leading everyone to the tracks.

* * *

Upon noticing how all the other guards were doing some quick warm ups and tying their laces up tightly, Castiel turned to Dean. "I believe the others are treating this exercise as a race." he told the green eyed man. "Yeah I know. So what do you say, do you wanna try and beat them?" Dean asked him, grinning. "Well I suppose that would be interesting to try." Castiel answered with deceptive calmness but the excited shine in his eyes gave it away.

Walking up to the start of the track, Cas quickly found a spot for them and practically dragged Dean towards it. Chuckling, Dean let himself get pulled to that spot. Castiel was surprisingly strong, but it was probably necessary to be strong in order to be a prison guard. Charlie and Pete made their way over to Cas and Dean, choosing the spot next to theirs. "Hey Cas!" the redhead greeted cheerfully. "Hello Charlie. Are you ready?" Castiel replied and Charlie grinned. "Ready to kick your ass? Yeah I am!" she answered, clearly pumped up about the exercise. "It's not a race." Cas reminded her at the same time Dean said: "We'll see about that." Charlie laughed. "I like this one. He's feisty. Keep him." she told Castiel, who turned red immediately. Laughing at Charlie's brash sense of humour and Castiel's embarrassment, Dean did a quick stretch before settling in a standard runner's stance. Copying his movements, Cas settled down next to him. "We're gonna have to work together and keep at the same pace since you've basically got me by the leash." Dean told him and Castiel nodded determinedly.

"On your marks." Cas could feel his heartbeat pounding in his ears, adrenaline building up inside of him. "Get set." Dean could feel Castiel gripping the handcuffs a little tighter. "Go!" Balthazar yelled and everyone took off running. Castiel was sprinting ahead and Dean was a little behind, his cuffs restraining him from any arm movements. "Slow it Cas!" he called out and almost immediately, Castiel slowed down so he was running beside Dean again. "Cuffs giving you problems?" Cas managed to ask. Dean nodded and felt the handcuffs being loosened a little bit. He should've been able to run faster but he saw how almost all the other pairs were ahead of them and he just couldn't get it in him to move any quicker.

"Dean. Pretend you're escaping and I'm chasing you." Castiel told him and suddenly Dean was back in that dim hallway again, running towards that exit, towards his freedom. This was like his second chance for it. He started speeding up and Castiel, also in that sense of déjà vu, chased after him determinedly. He pretended that his whole job was on the line if he didn't catch this prisoner. Dean bounded ahead, quickly passing Charlie, who was unfortunately partnered with Pete, who had no lower body strength. "Come on! Hurry!" she was yelling at Pete, who had stopped to catch his breath. Castiel gave them a quick wave as he ran past them. _Man, that felt good._

Dean felt as if he haas never run so fast in his life. The wind was cooling him off, and alleviating the stings he got when the gravel flew up around him. He didn't stop once to look up back as he swiftly passed one, two, five, ten pairs. Castiel followed Dean closely, weaving past their latest target: prison guard Garth who had somehow wrapped his own wrist around Bela's handcuffs. He laughed out loud as he ran, feet pounding against the ground, sending gravel flying up everywhere.

Soon enough, on their last lap, they caught up to the pair who had been reigning their position at first for fourteen laps. It was no one other than Gabriel and Raphael. Rapahel, or 'Gorilla Fists' as the inmates as well as some guards referred to him as, was basically dragging a poor Gabriel behind him. Gabriel was obviously tired, but he didn't open his mouth up once to gasp since there was dirt exploding upwards every two seconds. Smirking, Dean put on a final burst of speed and blurred past them, making sure to kick up an extra shower of gravel in Gabriel's direction, leaving them in the dust, literally. He heard Gabriel scream out a profanity and smiled to himself, pleased. _That'll teach him for trying to make a move on Sam._ Castiel, only a millisecond behind Dean, stifled a grin as he saw his brother and Raphael get sprayed with dirt, dust, and crushed rock.

As soon as Dean and Cas shot through the finishing line, the adrenaline and energy that had boosted them vanished. The two of them collapsed on a nearby bench, panting and gasping in gulps of oxygen. As soon as they were breathing normally again, two other pairs had finished and were either on benches or the grass, adjusting their breathing rates. Dean gave Castiel a grin, exhausted and was a little surprised when Castiel returned it. But this moment was short lived as a furious Gabriel stomped over to them, bits of gravel in his hair and muck on his face. "YOU!" he yelled, pointing an accusing finger at Dean. "What the hell was that for?" Castiel's brother exclaimed, livid. "What was what for?" Dean asked sweetly, playing innocent. "That freaking mud facial you gave me! No offence, but I prefer it to be done by spa professionals!" he screeched, trying to wipe some of the mud off. "No fighting!" Balthazar shouted from the other side of the field. "I'll get you back for this!" Gabriel warned Dean, and walked backwards to the other bench for dramatic effect.

Chuckling, Castiel turned to Dean. "Was it really necessary to bathe my brother in gravel?" he asked jokingly. "Hey, he wants to get to Sam, then he's gotta go through me." Dean replied, holding his arms up in mock defence.


	8. Chapter Eight

Dean stood in the middle of the cafeteria, holding a tray filled with barely identifiable foods, looking for a seat. He felt like he was in high school again, looking for a safe spot to eat at. His options were quite limited since there were only three groups the cafeteria was separated into. There were the guys he usually sat with, the big burly ones who had committed murders or much worse in the double digits. They were the stereotypical aggressive convicts but Dean sat with them because the only person he could tolerate, Benny, sat there too. But Benny had been shipped off to another block so Dean didn't see the point in sitting there anymore. Plus, he was no longer welcome to that group of tables anymore after he started a riot that caused them to have to go through gruelling and intense exercise. He also suspected he was shunned after beating up Alastair, who controlled most of the group. As if confirming his thoughts, Alastair's group all sent glares at him. Shrugging, Dean thought about joining the other convict group's table. They were the ones who were in here for petty crimes such as theft and they would definitely welcome him there since they were all afraid of convicts who were in prison for more than theft. The only problem was, Dean had a folded up page from his magazine and he wasn't about to let that get stolen from him. He turned to the last group that was sitting in the cafeteria, the guards and security. In fact, Charlie was grinning and waving him over to their table while Gabriel was scowling and trying to push her hand down. Dean was about to turn away when he saw Castiel entering the cafeteria, a small paper bag in hand. He noticed Dean and walked over to him. "If you're feeling unsure about where to sit, you can always sit with my friends and I." he told him, trying to be welcoming.

Uncertain, Dean thought about the pros and cons about sitting with the guards. The pros of sitting with them was that he had sort of friends over there and he wouldn't get anything stolen from him. But the cons were that if other prisoners saw him eating with them, they wouldn't be afraid of him anymore and he'd be neck deep in trouble. But guards were planted everywhere so Dean would be fine as long as he didn't wander off to anywhere without security cameras. God, he sounded like a pansy right now. Dean shouldn't need to depend on anyone, especially not people who wrongfully imprisoned him.

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Hi everyone! I am really, really, really sorry for the late update but school has been really stressful. I will try and update as much as I can but my schedule will be a little messed up! Anyways I hope you enjoyed this update!


	9. Chapter Nine

Dean watched hungrily as Castiel bit into his homemade peanut butter and jelly sandwich. Unaware, Cas took a sip of his apple juice and continued chewing. He was completely oblivious to Dean's longing stare at his lunch. That is, until Dean's stomach decided to embarrass him by growling very loudly. Quickly, he tried to quieten it by scooping up a spoonful of greyish mashed potatoes and swallowing it. Unfortunately, Dean didn't ingest it quick enough and his taste buds picked up the weirdly bland flavour of the food, if it could even be considered food.

Cas watched Dean make a face as he swallowed the tasteless cafeteria food. Feeling bad for some reason, he reached into his paper bag and fished out an apple. Castiel rolled the fruit over to Dean, who simply stared at it. "You can have my apple if you want. I know the cafeteria food isn't very good." he told Dean, who was still making no move to take it. Sighing, Cas grabbed it and held it out to him. "Dean, just take it. I already have a sandwich so you can have it." he assured him, still holding the apple. "Plus, I heard that the prison cafeteria food hasn't even passed the health examinations," Gabriel told them, his voice lowered to a loud whisper. "Apparently it violates three health codes!" he said to Dean, who was starting to believe him. "So you'll probably die really soon." Gabe continued and Castiel hit his arm. "That's not true at all." he reassured Dean, who had actually started believing Castiel's brother.

Dean eyed the apple hesitantly for a moment longer before accepting it. Taking a bite of it, he let the sweet juicy taste flood his mouth and wash away the awful taste of the mashed potatoes. "Thanks." Dean mumbled between bites and Cas smiled and shook his head. "It's no problem. And don't speak with your mouth full." he scolded the green eyed man lightly. Charlie set a small bag of pretzels in front of Dean. "Here, take this. I can't find a way to tell Dorothy that I actually hate pretzels." she told him, grinning playfully. Gabriel covered his food with his arms as a barrier. "Don't get any ideas." he glared at Dean who rolled his eyes. "Like any of your food is worth taking." he fired back and Charlie gave him a high five. Muttering to himself, Gabriel crammed another bite of his sub into his mouth, still scowling. Dean's hand hovered over the pretzel bag for a moment, unsure, before opening it.

He'd never thought he'd say this but Dean actually thought this lunch with the guards was probably the best one during his entire stay here. He laughed and chatted with them like friends and his lunch had never tasted better.

* * *

A few days had passed and Dean found the intensive training course not nearly as bad as the first time. It might have been because he had started to adapt or maybe because Castiel had started warming up to him. Or maybe even both. He was sitting at the table with Charlie, Cas, and Gabriel again like he had for the past few days and he was fully enjoying himself until one of the coaches, Balthazar decided to join them. "Mind if I join you?" the blonde man asked and set his food tray down on the table without an answer. An awkward silence filled the table. Well at least until Balthazar decided to speak up again. "God, this cafeteria food is terrible!" he exclaimed and grabbed a handful of pretzels from the daily pretzel bag that Charlie would give to Dean.

Annoyed, Dean cleared his throat. "Could you maybe ask next time?" he asked sarcastically. Balthazar raised an eyebrow. "Aren't you a convict? What are you doing here?" he queried, and though it seemed like he was simply asking an innocent question, Dean felt like he was taking a jab at his social standing. Castiel decided to cut in now. "Actually, he's my, I mean, _our_ friend and we invited him. There is also no rule that specifically says inmates can't sit with guards." he defended Dean. "That's true." Charlie agreed and Gabriel nodded as well. "And what's it to you? Don't you have some special seat for the coaches?" he retorted and Dean just sat there, shocked at who was defending him. The Ingram brothers, of all people. Balthazar, as it seemed, was also in shock. He grabbed his tray and stood up, probably trying to leave to avoid anymore humiliation. But before he left, he turned to Cas and Dean. "Good work today." he addressed them both but judging by the way his face softened, he was probably talking more to Castiel than to Dean. "Thank you." Castiel replied politely, the expression on his face reminding Dean of the stony one he had on when he first met him. Impressed with the way Cas was handling things, Dean turned to Balthazar as well. "Yeah, thanks." he said, not meaning it at all. His face hardening, Balthazar began to walk back to the coaches' table and Gabriel sighed in relief. "That tension might've actually killed me." he said, shaking his head. "Tell me about it." Charlie laughed and sipped her Coke. Dean took a bite of his pretzel and was about to add something when he noticed Castiel's disapproving look. Swallowing quickly, Dean joined in. "I felt like the tension was so thick, I wouldn't have been able to cut it with a chainsaw." he joked, and as the conversation drifted on, he stole a quick look at Cas. The blue eyed man was simply sitting there, eating his lunch, but there was definitely an unmistakeable smile on his face.


	10. Chapter Ten

Dean was grateful for how Castiel had defended him back there in the cafeteria. And not just against anyone. Against _Balthazar_ , one of the temporary staff members he's meant to get along with. He shouldn't have felt as grateful or pleased that Cas chose to defend him over Balthazar, but he did. That's why Dean was standing outside Uriel's office, waiting for the blue eyed guard to come out. But judging by Uriel's ranting, it didn't seem like Castiel would be coming out any time soon. Dean could hear everything that was being said and it was not pretty. Certain words were emphasised on during Uriel's speech, such as: irresponsible, idiotic, insubordinate, and a couple that were too vulgar to even mention.

After what seemed like hours, the door finally slammed and Dean quickly jerked his head up just in time to see a very pissed off Cas storming out. "I take it the meeting didn't go well?" he joked and the guard spun around, startled. "You're still here. You waited for me?" Castiel asked, looking surprised and _pleased?_ that he had stayed. Dean pushed himself off the wall, feeling a little embarrassed now for waiting. "Yeah, I thought this could be the least I do for you, considering Uriel just made your eardrums bleed for defending me." he replied sheepishly, rubbing the back of his neck. At the sound of Uriel's name, Cas' eyes narrowed again and his hands unconsciously balled into fists. "God, I wish Chuck would just come back and get rid of this guy." Dean nodded in agreement, unsure of what to say that could possibly comfort him. Then it hit him. The one thing that he was sure only he knew about Uriel. "Come on, I gotta show you something." he said, grabbing Castiel's hand and pulling him along.

It must have been a strange sight to see, a prisoner striding through the halls like he owned the place, with a confused guard in tow. "Where are we going?" the blue eyed man asked Dean, who was expertly weaving in and around people. The blond spared him a sidelong glance, wicked grin on his face. "Can't tell you. It's a surprise." Dean slowed down slightly to walk beside dark haired man and Cas turned to him. "Dean, I swear, if you try to pull another escaping stunt, I will not hesitate to tase you again." "Ooh kinky," he teased and quirked up an eyebrow suggestively, causing Cas' face to heat up. Dean laughed at the mortified expression on the guard's face. "Relax Cas, just a joke. I'm not trying to escape. Well not this time at least." he joked, earning a shove from the other man.

As they rounded a corner, Dean looked up to check that he was going the right way He had memorised a blueprint of this prison and he knew the building like the back of his hand, but he didn't want to end up getting lost on this expedition and end up in the wrong block. Block B, Level 3C. They're going the right way. "Alright, we're close." he told his companion, who had begun looking a little bored. "Now will you stop being so secretive and tell me where we are?" Cas whined and Dean grinned. "Okay, so there's this old office that Chuck used to use for private meetings and sometimes, Uriel likes to use it to-" "Winchester!" a loud voice echoed through the practically empty hallway as Gabriel came charging towards them. "Where do you think you're heading, taking my baby bro with you?" "I'm planning to escape and take Cas as a hostage." Dean answered sarcastically, not planning to let Cas' brother in on the mission. Gabe's eyes narrowed and he crossed his arms. "Quit bullshitting me Winchester and tell me where you're going or I'm just gonna assume you're off to find a nice closet for you and my brother to-" "Gabriel!" Castiel scolded, cutting him off. "What? Don't tell me you don't notice all those longing looks he gives you in the cafeteria!" the short man defended himself. Dean felt his face go red as he struggled to say a coherent sentence. "What?! I don't do that!" Gabe smirked at him. "Then what do you call those stares-" "Alright Gabriel that's enough!" Castiel inserted himself into the conversation again, this time, more firmly. "If you must know, Dean was going to take me to witness Uriel doing something embarrassing, not finding somewhere to have intercourse in." Dean shot Cas a disbelieving look. "You weren't supposed to say!" "Well I couldn't have kept it from my brother forever." Castiel responded.

"I want in."

Argument forgotten, both men looked at Gabriel. "No freaking way!" Dean denied immediately and Gabe looked towards Cas for help. "It _is_ Dean's secret and I've already broken one rule by telling you there was a secret in the first place." Castiel told him apologetically but at the sight of his brother's disappointed face, added: "You can be lookout though. Is that alright with you, Dean?" The two brothers turned to him and Dean was about to protest when he caught sight of Castiel's wide pleading eyes and softened a little. "Fine." he agreed begrudgingly and Cas brightened up. He didn't miss the way Gabriel smirked at him knowingly but pretended not to notice it. "See? You can come along." Castiel told his brother happily who, in turn, scowled. "Yeah, but I don't even get to go inside. I'm stuck with the suckiest and most boring job. Lookout. What kind of job is that? That's like the sucky job that's made up to keep the babies entertained and make them feel like part of the group." he complained, crossing his arms childishly. "You keep whining like a little bitch and you won't even get to be lookout." Dean warned him, effectively shutting Gabe up. "Just for the record," the short blond piped up again and Dean slapped his forehead. "I'm only shutting up because I want to and not because you told me to." "That's it." he said. "You're off the team." Of course, he didn't mean it but he really wanted to rile Gabe up again. The older Ingram brother's eyes widened comically and he started protesting. "What? That's not fair! You can't do that! I want to be part of the team!"

By now, Dean could barely keep the smile off his face as he exchanged glances with Cas, who had been listening to the conversation and was shaking with silent laughter. Gabriel realised he was being played and stopped objecting. "You bastard." he glared at Dean, who was outright laughing by now, and fought a smile from reaching his lips.

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Hello everyone and first off, I would like to start by apologising for not updating for such a long time! I am really really really sorry for delaying this but I was studying for my mocks, which I did crap at. Anyways, I know that that is no excuse for not updating so I will start posting more often again now that it's Christmas break! I hope you enjoyed this chapter!


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